(R)-tert-butyl 4-(3-(2,4-difluoro-5-(methoxycarbonyl)phenyl)-2-oxo-5-phenylimidazolidin-1-yl)piperidine-1-carboxylate | 1500113-90-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (R)-tert-butyl 4-(3-(2,4-difluoro-5-(methoxycarbonyl)phenyl)-2-oxo-5-phenylimidazolidin-1-yl)piperidine-1-carboxylate
• 英文别名: tert-butyl 4-[(5R)-3-(2,4-difluoro-5-methoxycarbonylphenyl)-2-oxo-5-phenylimidazolidin-1-yl]piperidine-1-carboxylate
• CAS: 1500113-90-5
• 化学式: C₂₇H₃₁F₂N₃O₅
• 分子量: 515.557
• InChiKey: VBMKQNMRQJLHQE-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  79.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (R)-tert-butyl 4-(3-(2,4-difluoro-5-(methoxycarbonyl)phenyl)-2-oxo-5-phenylimidazolidin-1-yl)piperidine-1-carboxylate 在 lithium hydroxide monohydrate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 0.75h， 以195 g的产率得到(R)-5-(3-(1-(tert-butoxycarbonyl)piperidin-4-yl)-2-oxo-4-phenylimidazolidin-1-yl)-2,4-difluorobenzoic acid
  参考文献：
  名称：

  Alkali Carbonate Effects onN-(2-Hydroxyethyl)ureaCyclization: Application to a 2-Imidazolidinone Scale-Up

  摘要：

  An imidazolidinone intermediate (3) used in the synthesis of novel HIV-entry inhibitors was prepared on multihundred gram scales in four steps and 40% overall yield. The penultimate step in the synthesis involved regioselective N-cyclization of N-(2-hydroxylethyl)urea (11) by in situ activation of the terminal hydroxyl group with p-TsCl in the presence of base. The ratio of N-cyclized to O-cyclized products followed a group IA periodic trend relative to the alkali carbonate base employed. The use of Cs2CO3 as base effected the desired N-cyclization with a high degree of regiocontrol (>98%).

  DOI：

  10.1002/jhet.1648
• 作为产物：
  描述：

  (R)-tert-butyl 4-((2-hydroxy-1-phenylethyl)amino)piperidine-1-carboxylate 在 caesium carbonate 、 对甲苯磺酰氯 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 (R)-tert-butyl 4-(3-(2,4-difluoro-5-(methoxycarbonyl)phenyl)-2-oxo-5-phenylimidazolidin-1-yl)piperidine-1-carboxylate
  参考文献：
  名称：

  Alkali Carbonate Effects onN-(2-Hydroxyethyl)ureaCyclization: Application to a 2-Imidazolidinone Scale-Up

  摘要：

  An imidazolidinone intermediate (3) used in the synthesis of novel HIV-entry inhibitors was prepared on multihundred gram scales in four steps and 40% overall yield. The penultimate step in the synthesis involved regioselective N-cyclization of N-(2-hydroxylethyl)urea (11) by in situ activation of the terminal hydroxyl group with p-TsCl in the presence of base. The ratio of N-cyclized to O-cyclized products followed a group IA periodic trend relative to the alkali carbonate base employed. The use of Cs2CO3 as base effected the desired N-cyclization with a high degree of regiocontrol (>98%).

  DOI：

  10.1002/jhet.1648